Acetic Acid Mixture with Hydrobromic Acid → HCID 23152740, compound

HRID 1012294Notes

Reaction equation

HRID 1012294 reaction equation
C([O:8][C:9]1[C:22]2[O:21][CH2:20][CH2:19][N:18]3[C:14](=[C:15]([CH:31]4[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]4)[C:16]4[CH:26]=[CH:25][C:24]([C:27]([O:29][CH3:30])=[O:28])=[CH:23][C:17]=43)[C:13]=2[CH:12]=[CH:11][CH:10]=1)C1C=CC=CC=1.Br.C(O)(=O)C>O>[CH:31]1([C:15]2[C:16]3[CH:26]=[CH:25][C:24]([C:27]([O:29][CH3:30])=[O:28])=[CH:23][C:17]=3[N:18]3[C:14]=2[C:13]2[CH:12]=[CH:11][CH:10]=[C:9]([OH:8])[C:22]=2[O:21][CH2:20][CH2:19]3)[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]1

Participants

4

Reactant 2

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 23152423HCID 23152423, compound

Product 1

HCID 23152740HCID 23152740, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To methyl 4-benzyloxy-12-cyclohexyl-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carboxylate (745 mg, 1.55 mmol) was added 25% hydrogen bromide-acetic acid solution (5 ml), and the mixture was stirred at room temperature for 30 min. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure. Hexane:diisopropy ether (3:1) solution was added to the obtained residue and the precipitated solid was collected by filtration. The solid was washed with hexane:diisopropy ether (3:1) solution. The obtained solid was dried in vacuo to give methyl 12-cyclohexyl-4-hydroxy-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carboxylate (470 mg, yield 78%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationAfter filtration
  5. customthe solvent was evaporated under reduced pressure
  6. additionHexane:diisopropy ether (3:1) solution was added to the obtained residue
  7. filtrationthe precipitated solid was collected by filtration
  8. washThe solid was washed with hexane:diisopropy ether (3:1) solution
  9. customThe obtained solid was dried in vacuo

Sources & evidence

ORD record
ord-b0ddeb780c7641148c4f9ae17db6a8fb
Source dataset
uspto-grants-2011_07
Patent number
US07977331B1

Reaction notes

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